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22nd August 2013 @ 08:57

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Reaction information

*#Reaction file  
CSRxnsScheme_83.cdx
*Reaction file type CDX
*Procedure  Dimethyl-2,2-di(oct-3-ynyl)malonate (1.52 g, 4.6 mmol), DMSO (12.0 mL), water (0.09 mL, 5.0 mmol) and LiCl (579 mg, 13.7 mmol) were stirred at 160 °C for 5 h followed by stirring at room temperature for 15 h.  The reaction mixture was diluted with water (75 mL) and extracted with ether (3 × 30 mL).  The organic extracts were combined, washed sequentially with water (2 × 50 mL) and brine (2 × 50 mL), dried (MgSO4), filtered and the solvent removed in vacuo to give the crude product as an orange oil (1.26 g).  Purification by column chromatography (SiO2, hexane/Et2O 10:1) gave the title compound as a colourless oil (1.10 g, 84%)
*Yield (%)  84
*Type of Yield Isolated product yield
Reference(s)  
AH Thesis_2011_pp58.pdf
AH Thesis_2011_pp145-167.pdf
Further information  Compound 83: Methyl-2-(oct-3-ynyl)dec-5-ynoate

For multistep reactions (or their steps):

Overall reaction? True
For overall reaction - links to child reaction steps  
For step in multistep reaction - link to previous reaction step  
For step in multistep reaction - link to following reaction step  
Attached Files
AH Thesis_2011_pp58.pdf
CSRxnsScheme_83.cdx
AH Thesis_2011_pp145-167.pdf